Isomeric phenylthioimidazo[1,2-a]pyridines as anthelmintics

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Abstract
A series of isomeric imidazo[1,2-a]pyridine-2-carbamates was prepared for testing as anthelmintics. The analogues were synthesized by reacting the appropriate 2-aminopyridine and methyl chloroacetylcarbamate. Steric hindrance in the 2,6-disubstituted derivative resulted in the formation of the isomeric 3-substituted analogue as the major product. Carbon-13 NMR proved useful in the structural assignments in this series. None of the analogues exhibited the potency of methyl 6-(phenylsulfinyl)imidazo[1,2-a]pyridine-2-carbamate when tested against Nematospiroides dubius in mice.